How does KAYAK find such low prices on flights from Hawaii to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Hawaii to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$209 CHEAP FLIGHTS from Hawaii to Chicago

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Cheap Flights from Hawaii to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Hawaii to Chicago

Mon, Apr 19 - Thu, Apr 29

2:12 pm - 6:00 amLIH Lihue-ORD Chicago O'Hare Intl

10h 48m1 stop Los Angeles

6:00 am - 12:22 pmORD Chicago O'Hare Intl-LIH Lihue

11h 22m1 stop Los Angeles

$424American Airlines

Thu, Jan 28 - Sun, Feb 7

1:50 pm - 5:56 amLIH Lihue-ORD Chicago O'Hare Intl

12h 06m1 stop San Francisco

8:40 am - 5:04 pmORD Chicago O'Hare Intl-LIH Lihue

12h 24m1 stop Denver Intl

$424United Airlines

Thu, Jan 28 - Sun, Feb 7

3:44 pm - 1:13 pmLIH Lihue-ORD Chicago O'Hare Intl

17h 29m2 stops Honolulu Portland

8:00 am - 5:14 pmORD Chicago O'Hare Intl-LIH Lihue

13h 14m1 stop Seattle/Tacoma Intl

$430Multiple Airlines

Thu, Jan 28 - Sun, Feb 7

9:46 pm - 6:00 pmLIH Lihue-MDW Chicago Midway

16h 14m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

9:38 am - 8:21 pmMDW Chicago Midway-LIH Lihue

14h 43m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

$435Delta

Thu, Jan 28 - Sun, Feb 7

9:46 pm - 4:26 pmLIH Lihue-ORD Chicago O'Hare Intl

14h 40m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

7:15 am - 8:21 pmORD Chicago O'Hare Intl-LIH Lihue

17h 06m2 stops Salt Lake City Seattle/Tacoma Intl

$435Delta

Thu, Jan 28 - Sun, Feb 7

9:30 pm - 4:25 pmLIH Lihue-MDW Chicago Midway

14h 55m1 stop Las Vegas Harry Reid Intl

9:55 am - 8:30 pmMDW Chicago Midway-LIH Lihue

14h 35m2 stops Oakland Honolulu

$503Southwest

Mon, Apr 19 - Thu, Apr 29

7:18 pm - 6:00 pmLIH Lihue-ORD Chicago O'Hare Intl

17h 42m2 stops Honolulu San Diego

8:00 am - 9:56 pmORD Chicago O'Hare Intl-LIH Lihue

18h 56m1 stop Seattle/Tacoma Intl

$518Multiple Airlines

Thu, Feb 18 - Tue, Feb 23

6:54 pm - 7:00 amOGG Kahului-ORD Chicago O'Hare Intl

8h 06mnonstop

11:45 am - 5:02 pmORD Chicago O'Hare Intl-OGG Kahului

9h 17mnonstop

$519American Airlines

Thu, Jan 28 - Tue, Feb 2

8:30 pm - 1:21 pmOGG Kahului-ORD Chicago O'Hare Intl

12h 51m1 stop Denver Intl

9:20 am - 2:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 20mnonstop

$528United Airlines

Wed, Jan 13 - Thu, Jan 21

11:10 pm - 4:45 pmOGG Kahului-MDW Chicago Midway

13h 35m1 stop San Diego

10:15 am - 8:25 pmMDW Chicago Midway-OGG Kahului

14h 10m2 stops Los Angeles Honolulu

$568Southwest

Recent last minute flight deals from Hawaii to Chicago

Tue, Nov 3 - Tue, Nov 10

11:15 pm - 5:25 pmHNL Honolulu-MDW Chicago Midway

14h 10m1 stop San Diego

5:50 am - 1:25 pmMDW Chicago Midway-HNL Honolulu

11h 35m1 stop Las Vegas Harry Reid Intl

$590Southwest

Thu, Nov 5 - Sat, Nov 14

11:09 pm - 6:59 pmHNL Honolulu-ORD Chicago O'Hare Intl

15h 50m1 stop San Diego

7:00 am - 4:30 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 30m1 stop Seattle/Tacoma Intl

$590Alaska Airlines

Tue, Nov 3 - Tue, Nov 10

11:15 pm - 5:30 pmHNL Honolulu-MDW Chicago Midway

14h 15m2 stops San Diego Las Vegas Harry Reid Intl

5:50 am - 1:25 pmMDW Chicago Midway-HNL Honolulu

11h 35m1 stop Las Vegas Harry Reid Intl

$596Southwest

Tue, Nov 3 - Wed, Nov 11

10:25 pm - 3:00 pmHNL Honolulu-ORD Chicago O'Hare Intl

12h 35m1 stop Seattle/Tacoma Intl

2:15 pm - 12:28 pmORD Chicago O'Hare Intl-HNL Honolulu

26h 13m1 stop San Diego

$610Multiple Airlines

Thu, Nov 5 - Sat, Nov 14

12:40 pm - 1:17 pmHNL Honolulu-ORD Chicago O'Hare Intl

20h 37m1 stop San Diego

7:00 am - 4:30 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 30m1 stop Seattle/Tacoma Intl

$620Multiple Airlines

Thu, Nov 5 - Sat, Nov 14

11:09 pm - 6:59 pmHNL Honolulu-ORD Chicago O'Hare Intl

15h 50m1 stop San Diego

7:00 am - 4:30 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 30m1 stop Seattle/Tacoma Intl

$620Alaska Airlines

Thu, Nov 5 - Mon, Nov 9

2:03 pm - 5:20 amLIH Lihue-ORD Chicago O'Hare Intl

11h 17m1 stop Los Angeles

12:42 pm - 10:30 pmORD Chicago O'Hare Intl-LIH Lihue

13h 48m1 stop San Francisco

$624United Airlines

Thu, Nov 5 - Mon, Nov 9

8:30 pm - 11:19 amLIH Lihue-ORD Chicago O'Hare Intl

10h 49m1 stop Denver Intl

10:25 am - 10:30 pmORD Chicago O'Hare Intl-LIH Lihue

16h 05m2 stops Los Angeles San Francisco

$630United Airlines

Thu, Nov 5 - Fri, Nov 6

7:00 pm - 7:27 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 27mnonstop

10:00 am - 3:18 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 18mnonstop

$645American Airlines

Thu, Nov 5 - Sat, Nov 14

7:00 pm - 7:27 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 27mnonstop

10:00 am - 3:18 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 18mnonstop

$651American Airlines

Useful Info

Low season	January
High season	November
Cheapest flight	$209

Best time to beat the crowds with an average 31% drop in price.

Most popular time to fly and prices are also 2% lower on average.

Flight from Honolulu to Chicago Midway Airport

How does KAYAK find such low prices on flights from Hawaii to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Hawaii to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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Complete your trip to Chicago with a hotel stay or car rental

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$209 Find Cheap Flights from Hawaii to Chicago - Compare and Save

Cheap Flights from Hawaii to Chicago

Recent round-trip flight deals from Hawaii to Chicago

Recent one-way flight deals from Hawaii to Chicago

Recent last minute flight deals from Hawaii to Chicago

Recent direct flight deals from Hawaii to Chicago

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Hawaii to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Hawaii

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Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight